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Article: Amino-functionalized pillar[5]arene

TitleAmino-functionalized pillar[5]arene
Authors
Keywordshost-guest systems
macrocycles
nanostructures
oxazoles
supramolecular chemistry
Issue Date2014
Citation
Chemistry - A European Journal, 2014, v. 20, n. 35, p. 10996-11004 How to Cite?
AbstractThe recently introduced pillar[n]arenes have provided chemists with receptors that, when incorporated into materials, confer unique properties upon them. The symmetrical rims and cylindrical shape of pillar[5]arene begs the question - can these pillar-like receptors be linked covalently end-to-end in order to create tubular structures by a growth-from-template approach? In our efforts to produce these one-dimensional extended structures, we have developed a new method of functionalizing pillar[5]arene in which one of the five hydroquinone units is converted into a diaminobenzoquinone analogue. The resulting diaminopillar[5]arene derivative, which undergoes a stereochemical inversion process that is slow on the 1H NMR timescale, can be chemically modified yet further in a direction that is orthogonal to the plane of its methylene bridging carbons through the formation of oxazole heterocycles. This strategy has been employed to create rigid oligomers that resemble one-dimensional tubular arrays. As a proof-of-principle, a rigid pillar[5]arene dimer has been isolated and characterized in the solution state as a 1:1 complex with an extended viologen for which it acts as a receptor. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/333090
ISSN
2023 Impact Factor: 3.9
2023 SCImago Journal Rankings: 1.058
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorStrutt, Nathan L.-
dc.contributor.authorZhang, Huacheng-
dc.contributor.authorSchneebeli, Severin T.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:16:40Z-
dc.date.available2023-10-06T05:16:40Z-
dc.date.issued2014-
dc.identifier.citationChemistry - A European Journal, 2014, v. 20, n. 35, p. 10996-11004-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/333090-
dc.description.abstractThe recently introduced pillar[n]arenes have provided chemists with receptors that, when incorporated into materials, confer unique properties upon them. The symmetrical rims and cylindrical shape of pillar[5]arene begs the question - can these pillar-like receptors be linked covalently end-to-end in order to create tubular structures by a growth-from-template approach? In our efforts to produce these one-dimensional extended structures, we have developed a new method of functionalizing pillar[5]arene in which one of the five hydroquinone units is converted into a diaminobenzoquinone analogue. The resulting diaminopillar[5]arene derivative, which undergoes a stereochemical inversion process that is slow on the 1H NMR timescale, can be chemically modified yet further in a direction that is orthogonal to the plane of its methylene bridging carbons through the formation of oxazole heterocycles. This strategy has been employed to create rigid oligomers that resemble one-dimensional tubular arrays. As a proof-of-principle, a rigid pillar[5]arene dimer has been isolated and characterized in the solution state as a 1:1 complex with an extended viologen for which it acts as a receptor. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.-
dc.languageeng-
dc.relation.ispartofChemistry - A European Journal-
dc.subjecthost-guest systems-
dc.subjectmacrocycles-
dc.subjectnanostructures-
dc.subjectoxazoles-
dc.subjectsupramolecular chemistry-
dc.titleAmino-functionalized pillar[5]arene-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.201403235-
dc.identifier.scopuseid_2-s2.0-84906783519-
dc.identifier.volume20-
dc.identifier.issue35-
dc.identifier.spage10996-
dc.identifier.epage11004-
dc.identifier.eissn1521-3765-
dc.identifier.isiWOS:000340902800018-

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